Ferric chloride hexahydrate: A convenient reagent for the oxidation of Hantzsch 1,4-dihydropyridines

被引:43
作者
Lu, J [1 ]
Bai, YJ
Wang, ZJ
Yang, BQ
Li, WH
机构
[1] NW Univ Xian, Dept Chem, Xian 710069, Peoples R China
[2] NW Univ Xian, Dept Chem Engn, Xian 710069, Peoples R China
关键词
D O I
10.1081/SCC-100105388
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and practical route for the moderate yield oxidative conversion of readily accessible 1,4-dihydropyridines (1,4-DHPs) to the corresponding pyridines was described using a relatively benign oxidant, i.e. ferric chloride hexahydrate (FeCl3. 6H(2)O). The reaction was carried out under mild and convenient condition. However, oxidation of 4-isopropyl-1,4-DHP lb with FeCl3. 6H(2)O afforded the dealkylated pyridine 2a.
引用
收藏
页码:2625 / 2630
页数:6
相关论文
共 23 条
[1]   MNO2 BENTONITE - A NEW REACTIVE FOR THE OXIDATION OF HANTZSCH DIHYDROPYRIDINES USING MICROWAVE IRRADIATION, IN THE ABSENCE OF SOLVENT .1. [J].
ALVAREZ, C ;
DELGADO, F ;
GARCIA, O ;
MEDINA, S ;
MARQUEZ, C .
SYNTHETIC COMMUNICATIONS, 1991, 21 (05) :619-624
[2]  
BOCKER RH, 1986, J MED CHEM, V29, P1596
[3]   Novel chemoselective and diastereoselective iron(III)-catalysed Michael reactions of 1,3-dicarbonyl compounds and enones [J].
Christoffers, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21) :3141-3149
[4]   UNUSUAL OXIDATIVE DEALKYLATION OF CERTAIN 4-ALKYL-1,4-DIHYDROPYRIDINES WITH MNO2/BENTONITE USING MICROWAVE IRRADIATION, IN THE ABSENCE OF SOLVENT(II) [J].
DELGADO, F ;
ALVAREZ, C ;
GARCIA, O ;
PENIERES, G ;
MARQUEZ, C .
SYNTHETIC COMMUNICATIONS, 1991, 21 (21) :2137-2141
[5]   ELECTRON-TRANSFER REACTIONS IN ORGANIC-CHEMISTRY [J].
EBERSON, L .
ADVANCES IN PHYSICAL ORGANIC CHEMISTRY, 1982, 18 :79-185
[6]  
GRINSTEINS E, 1967, GETEROTSIKL SOEDIN, P1118
[7]   OXIDATION OF DIHYDROPYRIDINE CALCIUM-CHANNEL BLOCKERS AND ANALOGS BY HUMAN LIVER CYTOCHROME-P-450 IIIA4 [J].
GUENGERICH, FP ;
BRIAN, WR ;
IWASAKI, M ;
SARI, MA ;
BAARNHIELM, C ;
BERNTSSON, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1838-1844
[8]   Substituted - Aromatic aldehydes in Hantzsch's pyridine condensation. Part II. Methyl- and nitro-benzaldehydes. [J].
Hinkel, LE ;
Ayling, EE ;
Morgan, WH .
JOURNAL OF THE CHEMICAL SOCIETY, 1931, :1835-1841
[9]   THE AROMATIZATION OF HANTZSCH DIHYDROPYRIDINES WITH NITRIC-OXIDE (NO) [J].
ITOH, T ;
NAGATA, K ;
OKADA, M ;
OHSAWA, A .
TETRAHEDRON LETTERS, 1995, 36 (13) :2269-2272
[10]   NEW DEVELOPMENTS IN CA-2+ CHANNEL ANTAGONISTS [J].
JANIS, RA ;
TRIGGLE, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (06) :775-785